Jump to main content
Jump to site search


Synthetic and mechanistic aspects of sulfonyl migrations

Author affiliations

Abstract

Over the past 20 years reports of sulfonyl migrations have appeared, frequently described as ‘unusual’ and ‘unexpected’. This comprehensive review compiles, for the first time, sulfonyl migrations reported over the last 20 years including formal 1,2-, 1,3-, 1,4-, 1,5-, 1,6- and 1,7-sulfonyl shifts, occurring through either radical or polar processes, either inter- or intramolecularly. Discussion of the sulfonyl migrations is structured according to reaction type, i.e. nitrogen–carbon, nitrogen–oxygen, nitrogen–nitrogen, oxygen–carbon (including anionic and non-anionic thia-Fries rearrangements), oxygen–oxygen and carbon–carbon migrations. Discussion of the underlying mechanisms for the migrations is included, with particular attention afforded to the principal techniques utilised for their elucidation, namely isotopic-labelling, crossover experiments, density functional theory calculations and electron paramagnetic resonance spectroscopy amongst others.

Graphical abstract: Synthetic and mechanistic aspects of sulfonyl migrations

Back to tab navigation

Article information


Submitted
04 Dec 2019
Accepted
03 Feb 2020
First published
03 Feb 2020

Org. Biomol. Chem., 2020, Advance Article
Article type
Review Article

Synthetic and mechanistic aspects of sulfonyl migrations

A. J. Flynn, A. Ford and A. R. Maguire, Org. Biomol. Chem., 2020, Advance Article , DOI: 10.1039/C9OB02587A

Social activity

Search articles by author

Spotlight

Advertisements